4-oxa-5-phenyl-7-octen-1-ol | 124389-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-oxa-5-phenyl-7-octen-1-ol
• 英文别名: 3-[(1-Phenyl-3-butenyl)oxy]-1-propanol；3-(1-phenylbut-3-enoxy)propan-1-ol
• CAS: 124389-41-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: JRLSRPGWDBTRNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-oxa-5-phenyl-7-octen-1-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 3-(1-phenylbut-3-enyloxy)propionaldehyde
  参考文献：
  名称：

  Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

  摘要：

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.055
• 作为产物：
  描述：

  4-phenyl-4-[3-(trimethylsiloxy)propoxy]-1-butene 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-oxa-5-phenyl-7-octen-1-ol
  参考文献：
  名称：

  Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

  摘要：

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.055

文献信息

• Facile Preparation of Allylzinc Species from Allyl Bromides and Unactivated Zinc Induced by a Catalytic Amount of Aluminum Chloride and Their Reactions with Carbonyl Compounds and Acetals.
  作者：Hatsuo MAEDA、Kazushige SHONO、Hidenobu OHMORI

  DOI：10.1248/cpb.42.1808

  日期：——

  The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3, was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α, β-unsaturated carbonyl compounds, selective 1, 2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavege also proceeded in excellent yields provided that two equivalents of AlCl3 was present.

  在干燥的四氢呋喃（THF）中，研究了路易斯酸（ZnCl2、AlCl3、BF3和TiCl4）对烯丙基溴和未活化的锌粉生成烯丙基锌物种的影响，并通过苯甲醛捕获有机锌化合物，即醛的格氏型烯丙基化反应。在所用的路易斯酸中，AlCl3被发现是最优的促进剂。在催化量的AlCl3存在下预形成的烯丙基锌物种能有效地烯丙基化羰基化合物。各种芳香族和脂肪族醛以及酮被转化为同烯丙基醇，产率良好至优秀。在所采用的反应条件下，酯、羟基、缩醛以及芳香族硝基和卤素基团均被容忍。对于α,β-不饱和羰基化合物，观察到了选择性的1,2-加成。取代的烯丙基溴如香叶基、巴豆基、肉桂基和2-环己烯基溴均能顺利转化为相应的烯丙基锌化合物，这些化合物与羰基化合物反应生成取代的同烯丙基醇，产率极佳。在巴豆基化、肉桂基化和2-环己烯基化中的立体选择性取决于有机金属和亲电试剂的结构。讨论了观察到的选择性的起源。在AlCl3的两当量存在下，伴随着碳-氧键断裂的二甲基和环状缩醛的烯丙基化也以极佳的产率进行。
• Allylation using allyborates
  作者：Roger Hunter、Joseph P. Michael、Geoffrey D. Tomlinson

  DOI：10.1016/s0040-4020(01)80802-4

  日期：1994.1

  A study has been carried out on the scope of allylation of a range of acetals activated by trimethylsilyl trfluoromethanesulfonate (TMSOTf) using a humber of organoborates. Intermolecular allylation of acyclic acetals proceeds smoothly and in high yield using lithium n-butyltriallylborate or lithium methyltriallylborate in THF at -78 degrees C while 1,3-dioxanes and dioxolanes give rise to some reduction products. Intramolecular allylation may be carried out via anchoring the triallylborane using an alkoxide anion. Mechanistic studies indicate that allyl transfer is from boron and not silicon, while stereoselectivity studies on the crotylation of acyclic acetals as well as the allylation of chiral acetals derived from (2R,4R)-pentanediol indicate moderate levels of diastereoselection.
• Allylation using organoborates and activated acetals
  作者：Roger Hunter、Geoffrey D. Tomlinson

  DOI：10.1016/s0040-4039(00)99638-2

  日期：1989.1
• HUNTER, ROGER;TOMLINSON, GEOFFREY D., TETRAHEDRON LETT., 30,(1989) N5, C. 2013-2016
  作者：HUNTER, ROGER、TOMLINSON, GEOFFREY D.

  DOI：——

  日期：——
• Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals
  作者：Suguru Ito、Akira Hayashi、Hirotomo Komai、Hitoshi Yamaguchi、Yoshihiro Kubota、Masatoshi Asami

  DOI：10.1016/j.tet.2011.01.055

  日期：2011.3

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.